Liquid Chromatographic Resolution of 3-Amino-1,4-benzodiazepin-2-one Derivatives on Various Pirkle-Type Chiral Stationary Phases

The two enantiomers of N-acyl amide and N-ureide derivatives of 3-amino-5-phenyl- 1,4-benzodiazepin-2-ones, which have been known to show anti-respiratory syncytial virus (RSV) activity, were resolved on seven different Pirkle-type chiral stationary phases (CSPs) with the use of 10% isopropyl alcohol in hexane as a mobile phase. Among the seven Pirkle-type CSPs, the one based on (S)-leucine derivative named as N-Phe-L-Leu was found to be most successful, the separation factors (alpha) and the resolutions (RS) for seven analytes being in the range of 1.78-4.21 and 5.94-15.08, respectively. By resolving N-benzyloxycarbonyl derivatives of 3-amino-5-phenyl(or 5-methyl)-1,4-benzodiazepin-2-ones on Pirkle-type CSPs, the phenyl ring at the 5-position and the N-H hydrogen at the 1-position of analytes were found to play an important role in the chiral recognition. Chirality 23: E16-E21, 2011. (C) 2011 Wiley Periodicals, Inc.